The documentary Fresh Dressed opens with vintage footage from a 1984 television pilot for a show called Graffiti Rock, which would have been hip-hop’s answer to Soul Train and a pop-cultural goldmine had it ever made it out of the incubation period. Instead, there was only the one episode, hosted by Basquiat cohort Michael Holman and featuring a performance by Run-DMC (with young Debi Mazar and Vincent Gallo dancing in the audience).

It’s the perfect starting point, however, for director Sacha Jenkins’ treasure trove of a doc, in which the music journalist and co-founder of ego trip magazine sets out to explore the evolution of hip-hop through the lens of fashion. In the process, he exposes the racism and classism at the root of so much creativity, and the crucial role that style played for anyone in poor and underprivileged communities who aspired to more. Such a conversation would not be complete without the artists and moguls who embody hip-hop’s ultimate triumph — from Kanye and Pharrell to Nas, Damon Dash, Swizz Beatz, and more — are here, offering insightful commentary on everything from poverty to Polo, and what it meant to dress like you had money even when you didn’t (a.k.a. fresh).

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But Jenkins also sat down with the even more compelling characters who watched and, in some cases, helped history unfold. Like Lorine Padilla, a former Savage Skulls member, who remembers a time when “police brutality was worse than it is today;” old-school b-boy legend Popmaster Fabel; and Dapper Dan, whose Harlem storefront sold knockoff luxury clothing and accessories in the Eighties to the likes of Mike Tyson and LL Cool J. (On their album Paid in Full, Eric B. & Rakim appear draped in his impostor Gucci leather.) This diverse assembly of artists, designers, hustlers, and everyday people walk us through history, making Fresh Dressed a thoroughly engaging documentary that transcends the subject of fashion and music. We talked to Jenkins on the eve of its Sundance premiere.

So what gave you the idea for Fresh Dressed?I moved to Astoria, Queens, from Silver Spring, Maryland, in 1977. I had a football — everybody else had Magic Markers and was breakdancing. I remember, growing up, how important it was how you dressed in a neighborhood where people didn’t have a lot. Like Damon Dash says, “When you live in an apartment with roaches and stuff, what else do you have?” You have your appearance. So I felt like fashion was a really powerful way to tell the backdoor story of hip-hop. In the South Bronx in the Seventies, an important part of being a gang member was having this jacket that you made on your own. Flash forward to the same neighborhood in 2014 and kids are getting killed for $600 jackets from brands they can’t even pronounce. I wanted to look at the evolution of where hip-hop has gone.

In which era do you feel like you have the earliest memory of fashion being as relevant as it is?I came up at a very pivotal time. After the gangs started to fade, there was that same impetus to make these sweatshirts where you iron on the letters that represented your name or your crew. We spray-painted our jean jackets. By 1985, crack hit, and I was still into graffiti. Kids in my hood looked at me like I was crazy because they’re making $800 a day selling drugs. Writing graffiti or spinning on your back made no sense. The film jumps from era to era, but if you pay attention, you can see how fashion went from this thing that represented who you were as a gang member to who you were as a crew member, and then it went to commerce.

So you have the rise of a guy like Dapper Dan, who said that a roll of fabric could be whatever he wanted it to be. That’s what hip-hop was. These kids didn’t have instruments, so a turntable went from being a tool to being an instrument. Dapper Dan did the same thing. He comes along and remixes clothing, and takes things that weren’t meant for him or his community and puts his spin on it — or as he said, “blackenized” it.

Nas says Dapper Dan was Tom Ford before Tom Ford — that he should have been hired, not shut down. Do you agree? His legacy is a little more complicated, because he did benefit from the crack epidemic.I think it’s just in line with the black experience in America. What is soul food? Soul food came from what the slaves ate. And what did the slaves eat? The scraps. It’s a part of the narrative of being in a tight situation as a person of color in America and using your resources to create a new narrative. Yeah, it’s complicated. Dan was using patterns and brands that didn’t belong to him. But the idea of these belts and hats, damn right, those are things that a creative director like Tom Ford gets paid top-dollar to do. The Smithsonian and other major institutions are seeking out and collecting [Dan’s] pieces. They’re one-of-a-kind masterpieces.

Are you skeptical or critical of luxury brands that might have ignored or disassociated themselves from hip-hop artists in the very beginning because they weren’t the target customers then?Can you really be mad at Ralph Lauren if he is just really great at focusing in on his audience, and his audience is technically an aspirational white lifestyle? He was a nice Jewish boy from the Bronx. A lot of the imagery around the stuff that he created — those worlds weren’t necessarily open to him. This is capitalist America. Black people and Latino people will spend money they don’t have on expensive items, just like white Americans do. That said, I don’t expect brands to change what they’re doing to pander to people. Louis and Gucci and Prada — they just stick to their script. Their script caters to a very specific audience. Just like Rocawear and Sean John catered to a very specific audience.

This is capitalist America. Black people and Latino people will spend money they don’t have on expensive items, just like white Americans do.

The film makes the point that some brands, like Cross Colours and Kani, in the long run didn’t achieve the success of luxury brands. Damon Dash says, “Most urban people really don’t want things made by other urban people. They want things they can’t attain.”It’s a combination of things. Fubu and Cross Colours and Sean John — what they were selling was a uniform. If you bought the Rocawear clothing, the idea was you were wearing the Jay Z uniform. But he’s not wearing Rocawear. He’s wearing the stuff that no one can pronounce. The real success is in brands where people are playing water polo and on yachts, all these aspirational things. I think that speaks to the power of white supremacy, and unfortunately, folks of color in America having extremely low self-esteem. “Well, why am I going to help Jay Z get rich? He’s not doing anything for me.” Instead of having the philosophy that he’s one of us, he’s from my community, and I want to support his brand.

Did you want to or try to talk to anybody at labels that over the years have been embraced by hip-hop artists, like Polo or Louis Vuitton?I knew that question was going to come up. It’s not like someone from Ralph Lauren said no, we’re not speaking to you because this is about hip-hop and black people. But neither of those key brands that are mentioned in the film wanted to participate in the discussion. So on one hand, it would have been powerful to hear from them, especially someone like Ralph. The love and respect that these kids, who had nothing at the time, had for Ralph Lauren — they know his entire life story. They know his real name is Lifshitz. They know he was able to transcend so much and create this rich, lush lifestyle.

But at the same time I also feel proud that the film is largely coming from a perspective that is unheard. It strikes a decent balance between the folks we all know and the folks we don’t. I didn’t just want it to be celebrities telling you about fashion and hip-hop. Hip-hop started with the people.

Do you think fashion now is as interesting and as expressive as it used to be?As some people have said, fashion might have reversed to the way it was, where it was all about originality and being an individual. The rappers still have this heavy influence but the difference between now and the Eighties is, yeah, you had successful rappers back then, but not on the level of Jay and Pharrell and Kanye. They’re moguls. Your average kid wants to be them.

And also the Internet. I was a black kid into hip-hip and breakdancing and graffiti, but I was also into hardcore and rode a skateboard. I was walking down the street some years ago, I had a Black Flag T-shirt on, and this young white guy tried to diss me: “What do you know about Black Flag, sir?” And I’m thinking, dude, you have no idea what my history is. That wouldn’t happen now. I see blacks kids wearing Black Flag shirts and riding skateboards all the time. Because of the Internet, everything is smaller. Everyone knows a little something about everything else. And fashion is a reflection of that.

Is there someone whose look you feel is very singular or original now?Well, that’s the funny thing, I’m not necessarily the fashion guy. It’s not really about the look. It’s about the idea behind the look. The film is about people who weren’t accepted in mainstream culture, or in outlaw culture, or in music culture. So they just said, “Hey, let me do my own thing.” To me, that’s what’s most important. It’s not about how original or cool you’re dressing. It’s what propelled you to do that. What I notice now is kids have references from so many different generations. When I was growing up, the Sixties were cool. Now it’s uninhibited — there’s no stopping where the influences come from. Fashion is only going to get wackier.

Check out our Sundance page for complete coverage of the 2015 festival.